(2S,4S,6R)-ethyl 4-hydroxy-6-(naphthalen-2-yl)-4-phenyltetrahydro-2H-pyran-2-carboxylate | 1402854-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,6R)-ethyl 4-hydroxy-6-(naphthalen-2-yl)-4-phenyltetrahydro-2H-pyran-2-carboxylate
• 英文别名: ethyl (2S,4S,6R)-4-hydroxy-6-naphthalen-2-yl-4-phenyloxane-2-carboxylate
• CAS: 1402854-16-3
• 化学式: C₂₄H₂₄O₄
• 分子量: 376.452
• InChiKey: XTKWYOVOBNTBKN-GPXNEJASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-萘甲醛 、 ethyl (S)-2-hydroxy-4-phenylpent-4-enoate 在 iron(III) chloride 、 叔丁基二甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以82%的产率得到(2S,4S,6R)-ethyl 4-hydroxy-6-(naphthalen-2-yl)-4-phenyltetrahydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Completely OH-Selective FeCl₃-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans

  摘要：

  The completely OH-selective Prins cyclization has been realized from the enantioselective ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated via FeCl3-catalyzed Prins reaction. Excellent stereoselectivities (up to >99:1 dr and >99.5:0.5 er) were obtained for a remarkably broad range of substrates under mild reaction conditions. The control experiments, including NOE effects and O-18-labeling studies, as well as DFT calculations were conducted to provide fundamental insights into the mechanism of the reaction. A different [2 + 2] cycloaddition process was suggested to rationalize the observed OH-selectivity.

  DOI：

  10.1021/ja3062002

文献信息

• Completely OH-Selective FeCl₃-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans
  作者：Ke Zheng、Xiaohua Liu、Song Qin、Mingsheng Xie、Lili Lin、Changwei Hu、Xiaoming Feng

  DOI：10.1021/ja3062002

  日期：2012.10.24

  The completely OH-selective Prins cyclization has been realized from the enantioselective ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated via FeCl3-catalyzed Prins reaction. Excellent stereoselectivities (up to >99:1 dr and >99.5:0.5 er) were obtained for a remarkably broad range of substrates under mild reaction conditions. The control experiments, including NOE effects and O-18-labeling studies, as well as DFT calculations were conducted to provide fundamental insights into the mechanism of the reaction. A different [2 + 2] cycloaddition process was suggested to rationalize the observed OH-selectivity.